Potassium Carbonate → (S)-4-glycidyloxy-N,N-dimethylbenzo(b)thiophene-2-carboxamide
Reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15]O)[C:7]=2[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC([N+]([O-])=O)=CC=1)(OC[C@H:29]1[O:31][CH2:30]1)(=O)=O>CN(C=O)C>[CH2:15]([O:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]([N:2]([CH3:17])[CH3:1])=[O:4])[S:9][C:8]=2[CH:10]=[CH:11][CH:12]=1)[C@H:30]1[O:31][CH2:29]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of N,N-dimethyl-4-(hydroxymethyloxy)benzo(b)thiophene-2-carboxamide (9.0 g) in DMF (100 ml) was added potassium carbonate (8.0 g), and (S)-glycidyl nosylate (8.0 g) was further added. The mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate to give the title compound (7.5 g).
Workup
- additionwas further added
- concentrationThe reaction mixture was concentrated under reduced pressure and water
- additionwas added
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained crystals were recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-2b67132adc8042ac843d0737ab80b740
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196199B2
Reaction notes
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